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Home » 11 of Carolyn Bessette-Kennedy’s best fashion moments
11 of Carolyn Bessette-Kennedy’s best fashion moments
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11 of Carolyn Bessette-Kennedy’s best fashion moments

News RoomBy News RoomFebruary 19, 20261 ViewsNo Comments

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2026-02-19T16:07:01.276Z




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  • Before her death in a plane crash, Carolyn Bessette-Kennedy was a well-known fashion icon.
  • As the wife of John F. Kennedy Jr., she was frequently photographed at glamorous events.
  • Bessette-Kennedy’s style is practically a main character in “Love Story.”

Arguably, no one can nail classic, “cool-girl” style quite like Carolyn Bessette-Kennedy did.

Bessette-Kennedy shot to prominence in the mid to late ’90s as the girlfriend and then the wife of John F. Kennedy Jr., the son of former President John F. Kennedy and Jacqueline Kennedy Onassis.

John F. Kennedy Jr., Carolyn Bessette-Kennedy, and her older sister, Lauren Bessette, were killed in a plane crash on July 16, 1999. There were no survivors from the accident, which happened off the coast of Martha’s Vineyard.

Before her passing, Bessette-Kennedy was known as a fashion icon, thanks to her minimalist outfits, which embodied what we now call the quiet-luxury aesthetic and featured a color palette of mostly black, white, beige, and navy blue.

Her personal style is now coming back into the zeitgeist with the release of Ryan Murphy’s “Love Story,” which chronicles the couple’s seven-year relationship.

Here are 11 of Carolyn Bessette-Kennedy’s best, most timeless looks.

Carolyn Bessette-Kennedy defied the fashion “rule” that you can’t mix black, brown, and beige.

Pictured here with John F. Kennedy Jr. in front of their Tribeca apartment in New York City, Bessette-Kennedy embodied classic autumnal fashion by pairing patent-leather brown boots with a simple black sweater and a camel-colored, calf-length skirt.

She accessorized with an understated black-leather bag and swept her blonde hair back into a low ponytail.

Before she married John F. Kennedy Jr., she was a publicist at Calvin Klein, which appeared to influence her personal style.

Bessette-Kennedy knew how to ace perfectly tailored, classic pieces similar to the ones Klein is known for, like this structured white button-up and black mermaid-tail skirt.

Vogue called this minimalist look “the epitome of uptown glamour without compromising her pared-back aesthetic.”

She largely stuck to a basic black palette for formal events.

Pictured here with her husband at the Municipal Art Society Gala in 1998, Bessette-Kennedy wore a strapless black column gown, velvet gloves, and pointed strappy stiletto heels.

However, for an off-duty look, she didn’t shun color altogether.

In 1996, while walking around New York City, she was photographed wearing a flowy summer dress with a bright floral print, black strappy heels, and a black, patent-leather handbag.

She looked effortlessly cool in a pair of perfectly tailored jeans and strappy sandals.

This classic look, from the black sleeveless tank to the brown-and-cream heeled sandals, would still be stylish now.

She often accessorized with a pair of sunglasses.

These rounded black sunglasses paired with a black button-up and green cargo pants epitomized ’90s fashion.

She was also the master of a classic coat.

While heading to the airport to catch a flight for Bill Clinton’s inauguration in January 1997, Bessette-Kennedy was photographed wearing a camel-colored skirt, black leather boots, and a belted black suede coat.

Nothing screams classic New York style like a pair of jeans, a white T-shirt, and a black leather jacket.

She finished the look with a tortoise-shell headband and a pair of oval sunglasses.

Even for events, she leaned into structured outerwear.

When attending the Newman’s Own George Awards in 1999, she paired a black coat with ruffled detailing with simple black pants and strappy heels.

Even when walking around New York City, she upgraded an otherwise casual look by choosing designer pieces.

In this 1996 ensemble, she layered a grey Miu Miu dress beneath a sleek black coat, striking a balance between understated elegance and effortless cool.

Tall black boots elongated the silhouette, while a glossy patent-leather bag added a more playful touch.

Carolyn Bessette-Kennedy will always be remembered as a fashion icon.

Bessette-Kennedy effortlessly blended elegance and simplicity in her fashion, becoming one of the decade’s most recognizable style icons.

There’s no arguing that Bessette-Kennedy, through her iconic minimalist style, made a lasting impact on the fashion world. She showed that while fast-fashion trends come and go, simple elegance lasts forever.



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